I wish I could have afforded holidays like that when I was young enough and fit enough. Now I'm retired and (via my wife's inheritance) wealthy enough, I'm too old and unfit (knees!) to do it!
As someone wiser than I once said, "Wealth is wasted on the rich."
In our case, we're not wealthy but found The Big Loophole. She's a teacher and after our trips to Europe about a decade ago (which we saved years to afford, mind you), started applying like mad for teaching abroad positions. Lived in Paraguay for 3 years, opening up Brazil and "The Cone" of South America, now live in Bogota.
Which means a 4-night trip to Medellin, flight, lodging, food, beer and daytrips cost less than one ticket from Arizona to Europe. Our airBNB in Quito, a really nice 1br apartment on the 10th floor of a new building was something like $42/night. So we're able to do a hell of a lot more for a heck of a lot less.
I telecommute so "have wifi, can work"... still logged a good amount of hours in the mornings during our trips.
While the travel is great, the lifestyle is not without sacrifices. Everything I own, minus TV, PS4 and washer/dryer fits into two suitcases, a proper hiking backpack and my carry-on luggage. If it doesn't, well, adios to something. Bogota has a lot more going for it as a place than Asuncion, but as a city of 9m or so, after six months I still feel entirely anonymous. About this time in Paraguay I was hitting stride and, thanks to the one remaining adult Blue in country, started making friendships that will last. Any night I wanted to hit The Hop, I knew I had friends there. Here, the closest I have are the guys at the tienda (bodega/minimart) next door warmly greeting with with the "AMERICA!" welcome when I come in for water or Aguila (beer-flavored water.)
And watch the (knees!) comment. After 3.5 years in South America, we finally booked a trip to Machu Picchu for June... and my knee has been acting up. Just an annoying twinge walking about town... but walking about town isn't 10km a day up and down hills at 3,000meters+ altitude.